metahexestrol dimethyl ether | 68266-30-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: metahexestrol dimethyl ether
• 英文别名: 3,4-di-(3'-methoxyphenyl)-hexane；3,4-Bis-(3-methoxyphenyl)-hexan；1-[1-Ethyl-2-(3-methoxyphenyl)butyl]-3-methoxybenzene；1-methoxy-3-[4-(3-methoxyphenyl)hexan-3-yl]benzene
• CAS: 68266-30-8
• 化学式: C₂₀H₂₆O₂
• 分子量: 298.425
• InChiKey: NRKKAHRTDAOAHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  metahexestrol dimethyl ether 在 三溴化硼 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 8.5h， 生成 meso-3,4-bis[4-[(dimethylamino)methyl]-3-hydroxyphenyl]hexane
  参考文献：
  名称：

  环取代的1,2-二烷基化的1,2-双（羟基苯基）乙烷。2.4，4′-，5，5′-和6，6′-二取代的间己烯醇的合成和雌激素受体结合亲和力。

  摘要：

  乳腺肿瘤抑制抗雌激素间己雌酚[间位-3,4-双（3-羟苯基）己烷]的对称的4,4'-，5,5'-和6,6'-二取代衍生物的合成是（1） [4,4'-取代基：F，（2），Cl（3），Br（4），I（5），CH2N（CH3）2（6），CH3（7），CH2OCH3（8），CH2OC2H5 （9），CH2OH（10），NO2（11），NH2（12），N（CH3）2（13），COCH3（14）和C2H5（15）; 5,5'-取代基：OH（16）和Cl（17）; 6,6'-取代基：OH（18），F（19），Cl（20）和CH3（21）]。1-3、16和19的合成是通过将苯乙酮与TiCl4 / Zn还原偶联，然后将顺式3,4-二苯基己-3-烯烯氢化而完成的。通过将1-苯基-1-丙醇与TiCl3 / LiAlH4偶联并分离内消旋非对映异构体，可以合成化合物17、18、20和21 而4-15是通过取代己雌酚

  DOI：

  10.1021/jm00371a004
• 作为产物：
  描述：

  1-氯-1-(3-甲氧基苯基)丙烷 在 乙基溴化镁 作用下， 以 乙醚 为溶剂， 以31%的产率得到metahexestrol dimethyl ether
  参考文献：
  名称：

  Potential antiestrogens. Synthesis and evaluation of mammary tumor inhibiting activity of 1,2-dialkyl-1,2-bis(3'-hydroxyphenyl)ethanes

  摘要：

  The syntheses of the meso-1,2-dialkyl-1,2-bis(3'-hydroxyphenyl)ethanes [alkyl substituent: CH3 (19), C2H5 (20), C3H7 (22), C4H9 (23), i-C4H9 (24), and C5H11 (25)] and of d,l-3,4-bis(3'-hydroxyphenyl)hexane (21) are described. In vitro these compounds inhibited the [3H]estradiol receptor interaction competitively, exhibiting Ka values between 0.20 x 10(9) (20) and 0.11 x 10(6) M-1 (24). In vivo the meso compounds reduced the estrone-stimulated mouse uterine growth; the most effective compounds were 20, 22, and 23 (53, 50, and 45% inhibition, respectively). Compounds 20 and 22-24 showed weak estrogenic activity in the mouse uterine weight test and in the vaginal cornification test. Compounds 19 (NSC-297169), 20 (NSC-297170), and 22 (NSC-297171) exhibited a dose-dependent growth inhibition on the MCF-7 human breast tumor cell line (10(-6) to 10(-9) M). These compounds also showed a marked dose-dependent inhibition on the DMBA-induced, hormone-dependent mammary carcinoma of the Sprague-Dawley rat corresponding to their association constants.

  DOI：

  10.1021/jm00142a014

文献信息

• Novel di-(3'-hydroxyphenyl)-alkane compounds, process of preparation and
  申请人：Klinge Pharma GmbH

  公开号：US04094994A1

  公开（公告）日：1978-06-13

  Compounds of di-(3'-hydroxyphenyl)-alkanes and their methyl ethers, of the formula ##STR1## wherein R is alkyl and R' is H or methyl, have activity against hormone-dependent breast carcinoma.

  二-(3'-羟基苯基)-烷烃及其甲醚化合物，化学式为##STR1##其中R为烷基，R'为H或甲基，对激素依赖性乳腺癌具有活性。
• HARTMANN, R. W.;BUCHBORN, H.;KRANZFELDER, G.;SCHOENENBERGER, H.;BOGDEN, A+, J. MED. CHEM., 1981, 24, N 10, 1192-1197
  作者：HARTMANN, R. W.、BUCHBORN, H.、KRANZFELDER, G.、SCHOENENBERGER, H.、BOGDEN, A+

  DOI：——

  日期：——
• SCHLOEGL, K.;WEISSENSTEINER, W., SYNTHESIS, BRD, 1982, N 1, 50-53
  作者：SCHLOEGL, K.、WEISSENSTEINER, W.

  DOI：——

  日期：——
• US4094994A
  申请人：——

  公开号：US4094994A

  公开（公告）日：1978-06-13
• Potential antiestrogens. Synthesis and evaluation of mammary tumor inhibiting activity of 1,2-dialkyl-1,2-bis(3'-hydroxyphenyl)ethanes
  作者：Rolf W. Hartmann、Helga Buchborn、Gerhard Kranzfelder、Helmut Schoenenberger、Arthur E. Bogden

  DOI：10.1021/jm00142a014

  日期：1981.10

  The syntheses of the meso-1,2-dialkyl-1,2-bis(3'-hydroxyphenyl)ethanes [alkyl substituent: CH3 (19), C2H5 (20), C3H7 (22), C4H9 (23), i-C4H9 (24), and C5H11 (25)] and of d,l-3,4-bis(3'-hydroxyphenyl)hexane (21) are described. In vitro these compounds inhibited the [3H]estradiol receptor interaction competitively, exhibiting Ka values between 0.20 x 10(9) (20) and 0.11 x 10(6) M-1 (24). In vivo the meso compounds reduced the estrone-stimulated mouse uterine growth; the most effective compounds were 20, 22, and 23 (53, 50, and 45% inhibition, respectively). Compounds 20 and 22-24 showed weak estrogenic activity in the mouse uterine weight test and in the vaginal cornification test. Compounds 19 (NSC-297169), 20 (NSC-297170), and 22 (NSC-297171) exhibited a dose-dependent growth inhibition on the MCF-7 human breast tumor cell line (10(-6) to 10(-9) M). These compounds also showed a marked dose-dependent inhibition on the DMBA-induced, hormone-dependent mammary carcinoma of the Sprague-Dawley rat corresponding to their association constants.